17,20,23-trioxa-4,12,14,26-tetraazahexacyclo[24.6.1.17,14.02,6.08,13.027,32]tetratriaconta-1(33),2(6),7(34),8,10,12,27,29,31-nonaene-3,5-dione

ID: ALA340935

PubChem CID: 10206423

Max Phase: Preclinical

Molecular Formula: C27H26N4O5

Molecular Weight: 486.53

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Indolylylmaleimide 1 | Indolylylmaleimide 1|CHEMBL340935|SCHEMBL1128191|BDBM50133059|17,20,23-trioxa-4,12,14,26-tetraazahexacyclo[24.6.1.17,14.02,6.08,13.027,32]tetratriaconta-1(33),2(6),7(34),8,10,12,27,29,31-nonaene-3,5-dione

Canonical SMILES:  O=C1NC(=O)C2=C1c1cn(c3ccccc13)CCOCCOCCOCCn1cc2c2cccnc21

Standard InChI:  InChI=1S/C27H26N4O5/c32-26-23-20-16-30(22-6-2-1-4-18(20)22)8-10-34-12-14-36-15-13-35-11-9-31-17-21(24(23)27(33)29-26)19-5-3-7-28-25(19)31/h1-7,16-17H,8-15H2,(H,29,32,33)

Standard InChI Key:  SYLBCDWZFLYHIX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.6167   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2917   -1.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.5167   -2.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1042   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5542   -5.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3625   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2167   -6.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5042   -3.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 36 26  1  0
 16 27  1  0
 31 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA340935

   INDOLYLYLMALEIMIDE 1

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 486.53

Molecular Weight (Monoisotopic): 486.1903

AlogP: 2.62

#Rotatable Bonds: ┄

Polar Surface Area: 96.61

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.71

CX Basic pKa: 3.38

CX LogP: 2.18

CX LogD: 2.18

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.38

Np Likeness Score: -0.42

References

1. Kuo GH, Prouty C, DeAngelis A, Shen L, O'Neill DJ, Shah C, Connolly PJ, Murray WV, Conway BR, Cheung P, Westover L, Xu JZ, Look RA, Demarest KT, Emanuel S, Middleton SA, Jolliffe L, Beavers MP, Chen X..  (2003)  Synthesis and discovery of macrocyclic polyoxygenated bis-7-azaindolylmaleimides as a novel series of potent and highly selective glycogen synthase kinase-3beta inhibitors.,  46  (19): [PMID:12954055] [10.1021/jm030115o]

2. Dessalew N, Bharatam PV..  (2007)  Structure based de novo design of novel glycogen synthase kinase 3 inhibitors.,  15  (11): [PMID:17399989] [10.1016/j.bmc.2007.03.048]

3. Freitas MP.  (2007)  A 2D image-based approach for modelling some glycogen synthase kinase 3 inhibitors,  16  (7): [10.1007/s00044-007-9086-8]

4. Winfield HJ, Cahill MM, O'Shea KD, Pierce LT, Robert T, Ruchaud S, Bach S, Marchand P, McCarthy FO..  (2018)  Synthesis and anticancer activity of novel bisindolylhydroxymaleimide derivatives with potent GSK-3 kinase inhibition.,  26  (14): [PMID:30026041] [10.1016/j.bmc.2018.07.012]

Source

Source(1):

• Scientific Literature